Recap / Monk S2E16 "Mr. Monk Goes to Jail"

We open in the execution chamber of a prison, where an officer tells Warden Christie that one Ray Kaspo's attempt to appeal his case has been overturned in federal court. In forty-five minutes, he'll be killed via lethal injection. Another inmate, Abernathy, is seen delivering Kaspo's requested last meal—an order of ribs and chili—to the holding cell. Kaspo tells Abernathy that he is at peace with what is about to happen, and even gifts his fellow prisoner his most precious possession—a set of drawing pencils—to pass onto his daughter. Abernathy thanks him and walks away...only to hear death throes a few moments later. He rushes back to the cell and finds Kaspo lying on the ground in agony, a frothy white substance oozing from his nose and mouth. Warden Christie comes running, but it is too late—Kaspo is dead...apparently forty-five minutes early.

The next day, Stottlemeyer summons Monk and Sharona to the prison to investigate the murder. All of Monk's phobias are immediately turned up to eleven at being in a prison, much to the frustration of Sharona and bafflement of the guards (especially when Monk offers to simply "frisk himself" rather than have anyone touch him). In the holding cell, Sharona suggests the most obvious solution—that the family of Kaspo's victims were trying to get revenge on him—but Monk discounts it, pointing out a letter from the family: they're Mennonites, who practice non-violence, and even mention that they've forgiven Kaspo and will pray for him. When Warden Christie reveals the central question of the crime—why murder a man who's already going to be executed?—Monk decides to cut and run: Kaspo was already doomed, and as his anxiety is becoming unbearable, there's no point in trying to solve the case. Before he and Sharona can leave, though, the gate guard receives a phone call and tells Monk that it's for him...

In a few moments, Monk and Sharona travel to the luxurious, fully-furnished jail cell of none other than Monk's Arch-Enemy Dale "the Whale" Biederbeck, the immensely fat criminal mastermind who is imprisoned thanks to the pair's efforts in an earlier case. Dale, in his ingratiatingly charming manner, freely admits that he summoned Monk, as he wants to make a deal with him. An unimpressed Sharona tries to usher Monk out, but Dale wins him back by promising to help him with his own troubles: "One hand washes the other. Now there's a metaphor I know you can relate to." Biederbeck explains that he has become the prime suspect in Kaspo's murder because of an unpaid debt—$1,200—that the younger man owed the financier. Monk immediately realizes that Dale wouldn't kill someone over what, to him, is pocket change; Dale agrees, but remarks that the cops don't see things that way. Furthermore, his status as a suspect means that he can't have a window installed in his cell wall. Dale proceeds to lose his mind with rage and tells Monk that he must solve the case for him, because he needs that window. Monk asks what Dale will give in exchange, and Biederbeck says the magic words: "What you want, Adrian. What you need. Information. You solve this murder...and I tell you everything I know about the man who killed your wife."

A while later, Monk has committed to solving the crime, despite Sharona pointing out that Dale could be lying, especially considering that Monk is the whole reason he was sent to jail in the first place. Monk explains that he can't give up—"This is for Trudy now." The pair's next stop is the kitchen where Kaspo's poisoned last meal was prepared. Warden Christie meets them and explains that Abernathy, who delivered the meal, and all of the cooks have been cleared. But Monk's keen eye notices that one of the cook's time cards was not punched out the previous night. The group investigates and discovers said cook, Tucker—or rather, his corpse—locked in the kitchen freezer. Monk tells an officer to search Tucker's pockets, where a fat wad of cash is sitting. The group now knows that someone paid off Tucker to slip the fatal poison into Kaspo's chili—but who? An answer comes in the form of Sylvia Fairborn, a social worker who serves as the prison's librarian. She tells Monk and Sharona that she overheard Kaspo in a heated argument with another inmate, Darnell "Spyder" Rudner. Kaspo apparently threatened to "tell the world" about a job the two pulled together in Calgary. It seems like Monk has a new lead, but problems immediately arise: Spyder is the meanest, cruelest, most violent prisoner in the whole compound, with four murders to his name and a history of beating up anyone who touches his stuff. Monk decides that the only thing to do is go undercover as a fellow inmate to try to get information out of Spyder. Sharona and Christie are against the plan, but Monk refuses to give up—"it's for Trudy."

We jump to Spyder being escorted out of solitary confinement, glaring down and frightening men twice his size along the way. He arrives in his cell and meets "Ben Lincoln," who's serving a five-year sentence for embezzling. Things get off to a terrible start, as Spyder immediately notices that Monk has rearranged his belongings and even touched his shiv. He's ready to rip the detective's head off...until Monk reveals that he sharpened the shiv, freshened the tape on the handle, and even relocated it to a better hiding place. That, plus a photo of Trudy on the wall, convinces Spyder that "Ben" isn't all that bad, and the two men begin to become friends. While they talk, Stottlemeyer and Disher head to Dale's cell to chat with him. He remains unimpressed by their supposed motive, but does admit that he's hired Monk for the case in the hopes of getting his window: "try living without one." Back in Spyder's cell, Monk fishes for information about Kaspo, but the larger man notices that his prized heirloom wristwatch has gone missing. Another fight seems imminent, but Monk quickly offers Spyder a deal: he'll track down who stole the watch if Spyder will tell him about Kaspo. Meanwhile, Sharona follows up her own investigation by going to the prison medical examiner's office. He reveals that Kaspo's death was particularly violent—the cocktail of chemicals he ingested liquefied his organs and was enough to kill ten men. He also mentions that someone's bound to be disappointed, as Kaspo was an organ donor with an extremely rare blood type ("AB negative with D antigen")—whoever was set to receive them is in trouble.

Monk and Spyder head for the prison yard, where a gang of Neo-Nazis immediately takes umbrage to Monk's presence. Before they can rearrange his face, though, he suggests that their leader return Spyder's watch—and sure enough, he's wearing it. Spyder is impressed by Monk's detective skills and keeps his word: he's not only never been to Canada, but he didn't even know Kaspo before prison. Monk and Sharona smell a rat and head to the prison library, where Sylvia seems shocked to see Monk alive...perhaps because she was hoping that Spyder would have killed him by now? Their inquiry is interrupted by an inmate complaining about what's playing on TV: an interview with local author James T. DeMornay whose recent book, Richer Than God, paints a scathing picture of reclusive billionaire Lambert Lawson. Lawson sued DeMornay for libel and would have completely bankrupted him, but in a lucky turn of events, Lawson recently died of kidney failure, meaning the suit has been thrown out. Sylvia hurries away, but not before Monk and Sharona notice the TV's remote hidden in her purse—she was clearly waiting for that interview.

While Sharona investigates this new lead, a guard receives a phone call from Warden Christie's secretary, asking Monk to meet him in the prison's Rec Room. Monk heads out...and we discover that the "secretary" was Sylvia, who smiles at the Neo-Nazis standing next to her. She tells them to go take care of Adrian, who ends up hemmed in on all sides by a group of violent skinheads out for his blood. Monk is able to hold them off with a sink's hose and rushes off. A blissfully unaware Sharona gets a call from Disher that confirms her theory about Lawson's blood type...AB negative with D antigen. As Sharona hangs up the phone, Warden Christie arrives. They realize that Monk is in serious danger and rush to the Rec Room. Along the way, Sharona, who has solved the case herself, gives The Summation: the true victim in the crime was not Kaspo, but Lawson. Kaspo shared Lawson's ultra-rare blood type, which meant that his kidneys were the only ones in the world that could possibly be transplanted into the billionaire's body. Since lethal injections attack the nervous system, the organs would have remained intact if Kaspo had been executed at midnight, so someone created a deadly poison to utterly destroy his kidneys (and the rest of his innards) instead. That someone is none other than Sylvia Fairborn—or, to use her married name, Sylvia DeMornay. James is her son, and she arranged the murder to keep him from being destroyed in court. Meanwhile, Monk's number is apparently up, as he's surrounded by the Neo-Nazis—only for Spyder to appear from nowhere and singlehandedly take them all on. His efforts save Monk's life, and the grateful detective promises to put in a good word for Spyder at his parole hearing (in about fifty years).

Back in Dale's prison cell, a window is finally being installed, and Sharona reminds the financier of his promise. After a brief moment of playing dumb, Dale agrees that "a deal's a deal" and begins to talk. His first revelation hits the hardest—Trudy herself was the target of the car bomb that killed her. Monk, who's spent years blaming himself for the murder as he believed that he was the intended victim, is stunned into silence as Dale mocks him: "I absolve you, Adrian Monk." Biederbeck then coyly remarks that he doesn't know why Trudy was targeted, and asks a seemingly unrelated question: "You ever been to New York?" He tells Monk that the man he's looking for—Warrick Tennyson, who was involved in the bombing in some way—will be found there. Sharona announces that if the answers Monk needs are on the East Coast, that's exactly where they'll go.

A while later, Monk, Sharona, Stottlemeyer, and Disher exit the jail. Monk claims that "prison changes a man," and Sharona quips that she certainly wishes that was the case. All seems well...until the final shot of the episode cuts to Dale alone in his cell, watching as a plane headed for New York flies by his window. He wickedly grins to himself: "Bon voyage, Mr. Monk..."

This episode includes examples of the following tropes:

• Alliterative Name: Lambert Lawson.
• All Men Are Perverts: Every single prisoner openly ogles after Sharona.
• AB Negative: Ray Kaspo's blood type—"AB negative with D antigen"—is called "the rarest in the world" and turns out to be the key to why he was murdered. This ties into...
• Artistic License – Biology: "AB negative with D antigen" isn't some kind of ultra-rare, precious blood type: in fact, it's just the opposite. People with AB negative, D antigen blood are actually universal recipients for any type of blood (negative blood can't have D antigens, so the phrase "AB negative with D antigen" is a fancy way of saying "AB positive").
• Artistic License – Law: Ray Kaspo was slated to donate his organs. In the United States, condemned prisoners cannot be organ/tissue donors. It's possible that since he was a billionaire, Lambert Lawson may have pulled some strings to ensure he got Kaspo's kidneys.
• Asshole Victim: Tucker, the chef who fatally poisoned Ray Kaspo, falls under this, as he himself ends up being murdered after doing so.
• Badass Boast: At the end of the episode, Sharona asks how Biederbeck was able to figure out vital clues about Trudy's death that no one else was ever able to find. His response is a bragging declaration—"Sweetheart, I am DALE the WHALE!"—reminding her that he's the (literal and figurative) biggest Information Broker in the world.
• The Bad Guy Wins: In a fairly downplayed fashion. Regardless of Adrian's involvement, Sylvia's plan succeeds flawlessly, in part due to just how fast and effective the poison is once the victim eats it. The Downplayed part comes from the fact that one of her victims was someone already scheduled to die, and her intended target was a fatally ill and remorseless billionaire who was going to sue her son into poverty because he criticized him in a book. No one beyond a close friend is really sad about either of them, but the method of death in both cases—deadly poison or a slow, painful illness—was horrid either way (even if it were necessary).
• Because You Were Nice to Me: Spyder Rudner at first thinks Monk was touching his stuff and threatens him. But he becomes okay with Monk after seeing how he made his bed, sharpened his knife (and showed a better hiding place for it) and, as a most appreciated gesture, found his stolen watch that his grandfather gave him. This pays off later, as Spyder saves Monk's life and was the one to tip him off that he was most likely being set up. Even after finding out Monk is (more or less) a cop, he shrugs it off and still chooses to defend him against other inmates trying to kill him.
• Berserk Button: Spyder Rudner, quadruple murderer and most feared inmate in the whole prison, has a famously Hair-Trigger Temper. But the one thing he hates more than anything is...people touching his stuff. And Monk ends up in the same cell with him. Everyone immediately assumes that Adrian is dead meat. Subverted, though, in that Monk uses his skills to clean the cell, sharpen Spyder's personal shiv, and even put it in a better hiding place. Spyder is genuinely impressed by him and lets him off the hook.
• Big Damn Heroes: Just when Monk is about to be taken apart by the Aryan Brotherhood, Spyder Rudner arrives and tells them to back off. When they attack, Spyder easily takes them both out and saves Monk's hide.
• Black Comedy: When Warden Christie takes Monk and Sharona into the kitchen, a sassy chef cracks jokes with them, saying that the food must be good because all of his diners are "repeat customers." The prison in general has a lot of guys using humor as a coping mechanism to deal with their situation.
• The Bus Came Back: Or more precisely, the bus stopped where Dale the Whale now lives, namely the prison where he's now serving a whole ton of life sentences.
• Cardboard Prison: Downplayed. The bars to Dale's cell stand wide open at all times. Of course, since Dale is almost completely immobile, he's not exactly an escape risk.
• Chekhov's Gunman: The members of the Aryan Brotherhood whom Monk falls afoul of during his time undercover end up being set up to kill Monk at the episode's climax. And then Monk ends up being saved from them by another Chekhov's Gunman, Spyder Rudner.
• Clear Their Name: Monk winds up having to clear his nemesis Dale's name of murder, in exchange for more information on Trudy's murder.
• Cool Teacher: Sylvia is portrayed as a caring teacher who is liked and respected by the vast majority of the inmates, although she turns out to be the killer.
• Cruel and Unusual Death: Ray Kaspo spends his last moments in excruciating agony as the poison in his last meal moves through his bloodstream. The coroner who does his autopsy remarks that the combined chemicals were powerful enough to kill ten men, and furthermore that Kaspo's organs weren't just damaged, they were liquefied (which, as it turns out, was the killer's goal all along, as she wanted to keep Kaspo from being able to donate his kidneys).
• A Day in the Limelight: Sharona really gets to shine in this episode. Since Monk is busy going undercover as an inmate, most of the police legwork falls to her, and she's even able to piece together exactly how and why Sylvia killed Kaspo thanks to her training as a nurse. When Monk tries to tell everyone his own findings, Sharona interrupts him: "I know, I already did the whole summation!"
• Do Wrong, Right: Monk shows Spyder a better hiding place for his knife (which he also fixes as he noticed it was dull and the handle was coming off), so the guards won't find it as easily. Spyder is legitimately impressed.
• Easily Forgiven: The family of the man Kaspo killed sends him a letter, telling him that they forgive him for murdering their son and are praying for his soul. Justified in that they are a Mennonite family, and that faith calls for complete pacifism.
• Even Evil Has Standards:
  • Spyder Rudner may be a violently destructive prisoner with at least four murders to his name, but even he thinks Neo-Nazis are the worst of the worst and sides with Monk, a cop, over them.
  • Parodied in-universe with Dale the Whale. He's a ruthless, sociopathic, horrible human being, but even he wouldn't kill someone over something as trivial as $1,200 ("I wouldn't bend down to pick up twelve hundred dollars—I mean, even if I could.").
• Evil Is Petty: Discussed; Dale doesn't care enough about the money that Kaspo owed him to have wanted him dead, but is bothered enough by the prospect of losing his new window to send Monk after the real killer.
• Gonk: Dale the Whale looks even more repugnant than during his debut appearance because of Dale's physical appearance deteriorating due to no longer having access to the expensive housekeeping and medical staff he had prior to his incarceration (well, that and them giving Tim Curry a more convincing Fat Suit than the one Adam Arkin had).
• Face Death with Dignity: At the beginning of the episode, Ray Kaspo is remarkably calm and has accepted what's about to happen to him, even telling the inmate who delivers his meal to let everyone know that he wasn't afraid as he waited for the lethal injection. It's then subverted when he spends his final moments in absolute agony as the poison hidden in his last meal liquefies his organs.
• Failed a Spot Check: Apparently, none of the prison staff noticed Tucker hadn't been brought back to his cell.
• He Knows Too Much: Presumably the reason why Sylvia killed Tucker (or had one of the Aryan Brotherhood members kill him) by locking him in the freezer.
• Hoist by His Own Petard: If Sylvia hadn't duped Monk into going after Spyder Rudner, he'd have had no reason to suspect she was involved in Kaspo's death. For good measure, Monk's getting in good graces with Spyder ends up saving his life when she sends the Aryan Brotherhood after him.
• I Gave My Word: After Monk fulfills his promise to solve Kaspo's murder and exonerate Dale, the financier remarks "A deal's a deal" and keeps his end of the bargain by sharing what he knows about Trudy's murder.
• Improvised Weapon: Monk finds himself stuck in the bathroom with a bunch of Neo-Nazis out for his blood. Just when they're about to start carving him open, he grabs the first thing he can—a sprayer from the sink—and uses it to blast their faces with hot water, buying himself enough time to escape.
• Jabba Table Manners: Dale shows off his cruel side by spitting the Chinese food a prisoner feeds him directly back onto his body, demanding that he microwave it.
• Karma Houdini: Lampshaded by Dale the Whale; he no longer has access to his fortune, and the surroundings and food aren't as nice as before. Regardless, he still has decent amenities and can eat food to his liking. If anything, he's still as much a prisoner of his own body as he was before he was convicted. The only difference is, there are restrictions to what he can ask for that's outside his prison.
• Only Known by Their Nickname: Everyone calls Darnell Rudner "Spyder".
• Locked in a Freezer: How Tucker, the inmate who poisoned Ray Kaspo, was killed.
• Luxury Prison Suite: Dale, largely thanks to his endless cash flow and connections, manages to turn what should have been a life sentence into a rather comfortable stay—he has a carpet, fine furniture and art, books, and access to a Chinese restaurant that delivers.
• Make an Example of Them: This is is Stottlemeyer's reason behind Dale the Whale's motive for killing Kaspo: while the loan he owed him was trifling, Biederbeck could have had him killed as a warning to anyone who might have tried to take advantage of him. Dale immediately shoots the theory down—even in prison, he's still one of the most feared criminals in the world, and everyone is firmly aware of the power he holds.
• Mama Bear: Sylvia Fairborn killed Kaspo because her son James wrote a book that criticized billionaire businessman Lambert Lawson. Lawson, who was terminally ill and desperately needed an organ transplant to live, promptly sued James for every penny he had; Sylvia reasoned that if Lawson died, the suit would be thrown out, and thus killed the one person who had the same rare blood type as Lawson and could have saved his life.
• Meaningful Name: Monk uses the alias "Ben Lincoln" for his prisoner persona, who's in jail for embezzlement. Ben (as in Benjamin Franklin) and Lincoln (as in Abraham Lincoln) both appear on U.S. currency.
• A Nazi by Any Other Name: Monk ends up having a run-in with the prison's Aryan Brotherhood group, first at the midway point of the episode, and then again at the climax.
• Nice Job Fixing It, Villain: The culprit tried to have Monk killed by convincing him that notorious inmate Spyder is a person of interest in the case. Monk goes undercover as Spyder's cellmate, and the two become friends instead. In the end when Sylvia tries to have Monk killed again (this time with some Neo-Nazi skinheads) Spyder comes to Monk's rescue.
• No Good Deed Goes Unpunished: In presumably an attempt to do at least one good thing before he dies, Kaspo gives his drawing pencils to Abernathy, to pass on to Abernathy's daughter. Kaspo gets fatally poisoned right afterward.
• Not Me This Time: The authorities intend to indict Dale the Whale for Kaspo's death, in part because Kaspo owed him $1,200 (which as much of a motive as they can find for anyone to kill him), and also because he's so hated and guilty of so many other crimes that no jury in the world would fail to convict him, no matter how circumstantial the evidence. Dale notes that normally he wouldn't care seeing how he's going to die behind bars either way, but getting an additional conviction at that particular moment will cause him to not get a new window installed in his cell.
• "Not So Different" Remark: Dale uses this twice over the episode by comparing himself to Monk.
  • When Monk first arrives in Dale's jail cell, the detective snarks at Dale's "poetic" comments about his enormous body being a kind of prison. Dale immediately fires back: "Well, of course it doesn't compare to the prison you've built for yourself." This clearly gets under Monk's skin, as he changes the subject instantly.
  • After Monk solves the case, he notes that Dale has finally received the window he so desperately wanted.
    Dale: Now I can see the world!...and yet, not be part of the world. Something else we have in common...
• Ooh, Me Accent's Slipping: In contrast to the two American actors who portrayed Dale in other episodes, Tim Curry's native English accent slips out at certain moments.
• Paper-Thin Disguise: Played with; Monk really sticks out like a sore thumb when he goes undercover in the prison, but manages to pass himself off as a white-collar criminal who ended up with a terrible lawyer, thus causing him to end up in the state penitentiary instead of the kind of minimum security "holiday camp" prison that such criminals usually end up at.
• Pet the Dog: By revealing the truth about Trudy's death—namely, that she herself was the victim, and not Adrian—Dale does a genuinely kind thing by relieving Monk of the tremendous guilt he's carried around for years. Dale lampshades the rarity of his doing anything remotely charitable after he tells the secret: "There's my good deed for the decade!" It's arguably a subversion, though, given that Dale wants Monk to learn more about Trudy's murder as part of a long-term revenge scheme.
• Pragmatic Villainy: Sylvia Fairborn is terrifyingly efficient when she needs to be. After her scheme to have Monk get on Spyder's bad side fails, she simply hires the Aryan Brotherhood members to kill the detective instead. She also uses simple but impossible-to-prove lies to lure people into traps.
• Prisoner's Last Meal: The episode begins with condemned prisoner, Ray Kaspo, being delivered his requested last meal—ribs and chili. However, it's discovered too late that someone had poisoned the food, and the prisoner dies in his cell before his scheduled execution. Monk is then brought in to investigate the crime scene and go undercover at the prison to find who would want to murder somebody who was about to be executed.
• Red Herring:
  • Spyder Rudner is this in-universe, with Sylvia trying to finger him as Kaspo's likely assailant and suggesting that Monk go undercover in the prison population, assuming that someone as obviously unsuited to prison life as Monk will get himself killed rather quickly.
  • The authorities and Monk are so busy looking for reasons why people would want to kill Kaspo himself that they fail to realize that Kaspo's murder was actually just a means to an end, namely so that a billionaire businessman would miss out on a liver and kidneys that would have been donated from Kaspo, and pass away himself.
• Tampering with Food and Drink: Ray Kaspo is killed with a poison that was slipped into his chili.
• The Reveal: The car bomb that killed Trudy Monk really was intended for her all along, rather than her being the accidental victim of an assassination attempt on Monk himself, as he had always assumed.
• Sequel Hook: The final shot of the episode is Dale looking out of his prison cell, as Monk and company fly to New York, setting up the following season's premiere.
• Sherlock Scan: Monk does this three times over the course of the episode.
  • During the initial investigation in Kaspo's cell, he immediately notices a letter from Kaspo's victim's family which forgives him, and furthermore sees from their address that they're from a Mennonite region of Pennsylvania, meaning that they weren't out for revenge.
  • When Monk and Sharona are in the kitchen searching for clues, Adrian spots a punch card with the previous day's date on it, meaning that its owner never clocked out the previous night. Sure enough, the missing cook—Tucker—turns out to be the one who slipped the poison into the fatal chili (although he didn't make it) and ended up dead for his trouble.
  • Monk is able to figure out who took Spyder's wristwatch by looking over the prisoners in the yard and immediately deducing which of them had long enough arms to reach into the cell and is wearing a long-sleeved shirt to cover up the stolen goods.
• Sympathy for the Devil: While Dale is, as always, a revolting human being with virtually no redeeming qualities, it's possible to feel a twinge of pity for him when he's denied a window in his jail cell—the one thing he desperately wants. It's telling that Dale drops his jovial facade when Stottlemeyer asks about it:
  Stottlemeyer: Is a window really that important to you?
  Dale: Try living without one.
• There Is No Kill Like Overkill: It's mentioned that the combination of poisons used to kill Kaspo utterly destroyed every organ in his body. It turns out that this wasn't just a case of someone wanting to inflict a Cruel and Unusual Death on him, however, but rather make it so that his organs couldn't be donated to anyone.
• Wham Line: Dale's revelation to Monk: "The bomb that took Trudy from you...was not intended for you. It was meant for her." This completely flips the series' overarching mystery on its head—for two seasons, Monk (and the audience) assumed that he was the target of the explosion that killed Trudy. Hearing that Trudy's death was the actual goal forces Monk to start delving into her past to figure out why anyone would want to kill her.
• You Are Worth Hell: Monk's claustrophobia and hatred of dealing with people are on full blast while he's in the prison, and when he finds out there's a chance to connect Spyder to the case, he goes undercover as a prisoner, despite Spyder's violent temper toward anyone who dares to touch his things. Why? Because Dale has promised to tell him what he knows about Trudy's death if Monk can prove him innocent, and Monk will risk everything for his wife. It's discussed by Spyder when he sees Monk staring at a photo of Trudy and realizes that she's his rock: "She keeps you strong."
• You Have Outlived Your Usefulness: Once Tucker had poisoned Ray's food, he was locked in a freezer to keep him from talking.

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